One-Pot Synthesis of Succinimide-3-Carboxamide Derivatives Using Microwave and Mechanistic Insights and Kinetics Analysis by Computational Method

In the present work, one-pot, four-component condensation of meldrum’s acid and acetonewith tert-butyl isocyanides in the presence of primary amines under microwave irradiationwhich provided 1-tert-butyl-4,4-dimethyl-2,5-dioxopyrrolidine-3-carboxamides in short timewith high yields have been investigated. Also, multiple mechanisms have been studied theoreticallyfor comparing formation of the amidosuccinimide with triamide products using abinitio molecular orbital theory in gas phase. The potential energy profile was constructed atthe HF/6-311G (d, p) level of theory. Among four speculative proposed path only the pathwayA (intramolecular reaction to formation amidosuccinimide product) was recognized as adesirable mechanism. Theoretical kinetics data involving k and activation parametres (Ea,ΔG‡, ΔS‡ and ΔH‡) were calculated for each step of the paths. In order to determine the possiblenucleophilic sites for the N17, N33 local reactivity has been evaluated through Fukuiindices.